Madonna, the iconic pop star, has recently made headlines with a surprising revelation about her past romantic encounters. In a video promoting her new album, “Confessions II,” the 67-year-old singer shared an unexpected secret that left everyone in the room stunned.
During the video, designer Raul Lopez asked Madonna, “Who was your best d— down?” Before answering, Madonna hesitated and said she would only name dead people. She then put a hand over her mouth and whispered, “John Kennedy Jr.”
The reaction from the group, which included Jeremy O. Harris, Bob The Drag Queen, Ivy Mugler, and Marcello Gutierrez, was one of shock. Lopez responded, “Everyone says his d— was crazy and he was a good f—…you’re the third person I’ve heard say that.” Madonna cheekily confirmed, “Mmm hmm.”
When Were Madonna and JFK Jr. Romantically Involved?
The couple had a brief fling in the late 1980s after Madonna split from her then-husband, Sean Penn. This information comes from the 2024 book, “JFK Jr.: An Intimate Oral Biography,” written by Liz McNeil and RoseMarie Terenzio. A friend of Madonna claimed in the book that “she came on to him and it was flattery.” Another pal alleged that Madonna was “totally a fling. Nothing more. Barely a fling at that.”
Christopher Andersen, who has written books on both JFK Jr. and Madonna, noted that the former attorney was “dazzled by the notion of dating Madonna, the most glamorous, celebrated and, by all accounts, exciting woman of her generations.”
JFK Jr. Wanted Madonna to Be His Cover Model
Years after their romance rumors, Kennedy requested that Madonna pose on the cover of his magazine, George. According to Terenzio, “John had this idea of having Madonna pose on the cover as his mom.” The plan involved dressing her in a suit, her signature sunglasses, and a pillbox hat sitting on a stack of books.
However, Madonna declined the offer and reportedly sent a fax that read, “Dear Johnny boy, Thanks for asking me to be your mother, but I’m afraid, I could never do her justice. My eyebrows aren’t thick enough for one. When you want me to portray Eva Braun or Pamela Harriman I might say yes! Hope you’re well. Love, Madonna.”
Inside Details on Madonna and JFK Jr.’s ‘Flirtation’
In July 2016, a friend of JFK Jr., who passed away at age 38 in 1999, shared more intimate details about the pair’s relationship. “It was a flirtation, and when other people referred to her as M around that time, just by her first initial, he would say, ‘I started that,’” the source shared. “He called her M when he wrote or faxed her. There were no cell phones then and he was always very territorial that he started that moniker for her.”
